Sodium Carbonate → HCID 46941129, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of [3-(5-Iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-yl)-phenyl]-dimethyl-amine (0.084 g, 0.226 mmol, 1 eq), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3-trifluoromethyl-pyridin-2-ylamine (0.098 g, 0.339 mmol, 1.5 eq), 2M aq Na2CO3 (1 mL) and PdCl2(PPh3)2 (0.032 g, 0.045 mmol, 0.2 eq) was heated at 110° C. for 24 h. The solvent was removed in vacuo and the residue was redissolved in DCM/water (150 mL) and extracted with DCM (2×80 mL). The organic layer was dried (MgSO4), filtered and evaporated. The residue was triturated from MeOH and filtered off. The solid was purified by column chromatography (0-5% MeOH in DCM) to give the desired product (15 mg, 16%) as a yellow solid. HPLC-MS (5-100% B in 8 min at 0.8 mL): tR=5.97 min, [M+H]+ m/z 405.1; 1H NMR (300 MHz, DMSO) δ 8.86 (d, J=1.8 Hz, 1H), 8.45 (d, J=2.0 Hz, 1H), 7.80 (s, 1H), 7.40 (t, J=8.1 Hz, 1H), 7.20 (m, 2H), 6.99 (dd, J=9.1, 2.0 Hz, 1H), 6.75 (s, 2H), 3.00 (s, 6H).

Provenance & Evidence